EP1229038A1 - Sels de borates pour utilisation dans les cellules électrochimiques - Google Patents

Sels de borates pour utilisation dans les cellules électrochimiques Download PDF

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Publication number
EP1229038A1
EP1229038A1 EP01130618A EP01130618A EP1229038A1 EP 1229038 A1 EP1229038 A1 EP 1229038A1 EP 01130618 A EP01130618 A EP 01130618A EP 01130618 A EP01130618 A EP 01130618A EP 1229038 A1 EP1229038 A1 EP 1229038A1
Authority
EP
European Patent Office
Prior art keywords
oder
lithium
salts
solvent
electrochemical cells
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP01130618A
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German (de)
English (en)
Inventor
Michael Dr. Schmidt
Andreas Dr. Kühner
Klaus-Dieter Dr. Franz
Gerd Dr. Prof. Röschenthaler
German Bissky
Alexander Dr. Kolomeitsev
Alexander Dr. Kadyrov
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Merck Patent GmbH
Original Assignee
Merck Patent GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Publication of EP1229038A1 publication Critical patent/EP1229038A1/fr
Withdrawn legal-status Critical Current

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    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
    • H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
    • H01M10/0566—Liquid materials
    • H01M10/0569—Liquid materials characterised by the solvents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES OR LIGHT-SENSITIVE DEVICES, OF THE ELECTROLYTIC TYPE
    • H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
    • H01G11/04—Hybrid capacitors
    • H01G11/06—Hybrid capacitors with one of the electrodes allowing ions to be reversibly doped thereinto, e.g. lithium ion capacitors [LIC]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES OR LIGHT-SENSITIVE DEVICES, OF THE ELECTROLYTIC TYPE
    • H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
    • H01G11/54—Electrolytes
    • H01G11/58—Liquid electrolytes
    • H01G11/62—Liquid electrolytes characterised by the solute, e.g. salts, anions or cations therein
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/052—Li-accumulators
    • H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
    • H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
    • H01M10/0566—Liquid materials
    • H01M10/0568—Liquid materials characterised by the solutes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/13—Energy storage using capacitors

Definitions

  • the invention relates to borate salts, processes for their preparation and their application in electrochemical cells.
  • Lithium-ion batteries are among the most promising systems for mobile applications.
  • the areas of application range from high-quality electronic devices (e.g. mobile phones, camcorders) to towards batteries for motor vehicles with electric drive.
  • These batteries consist of a cathode, anode, separator and a non-aqueous electrolyte.
  • a cathode typically Li (MnMe z ) 2 O 4 , Li (CoMe z ) O 2 , Li (CoNi x Me z ) O 2 or other lithium intercalation and insertion compounds are used as cathode.
  • Anodes can consist of lithium metal, carbons, graphite, graphitic carbons or other lithium intercalation and insertion compounds or alloy compounds.
  • Solutions with lithium salts such as LiPF 6 , LiBF 4 , LiClO 4 , LiAsF 6 , LiCF 3 SO 3 , LiN (CF 3 SO 2 ) 2 or LiC (CF 3 SO 2 ) 3 and mixtures thereof in aprotic solvents are used as the electrolyte.
  • the common lithium conductive salts show various disadvantages. Some conductive salts have low cycling yields (eg LiBF 4 ). Other conductive salts have low thermal stability (eg LiPF 6 ), and yet other conductive salts are not particularly suitable because of their toxicity and low environmental compatibility (eg LiAsF 6 ).
  • LiBF 4 would have a higher thermal stability than LiPF 6 . However, it forms electrolytes with very low ionic conductivity in aprotic solvents and is therefore less suitable for high-energy batteries.
  • imides in particular Bis (trifluoromethylsulfonyl) imide according to US 45054997
  • Methanides in particular Tris (trifluoromethylsulfonyl) methanide according to US 5273840 proposed.
  • These salts have a high anodic stability and can be used in organic aprotic solvents form high conductivity.
  • EP 929558 teaches the use of lithium fluoroalkyl phosphates with preferably perfluorinated ethyl or isopropyl groups.
  • the thermal stability, as well as the hydrolysis resistance of these lithium salts is significantly increased compared to LiPF 6 .
  • the present invention relates to salts for electrolytes, for use in electrochemical cells with high conductivity to provide that are electrochemically stable.
  • the invention relates to processes for producing these Compounds and their use in electrolytes for electrochemical Cells, batteries, double layer and supercapacitors.
  • Li [BF 3 (CF 3 )] and Li [BF 3 (CH 3 )] are, for example, in pure diethylene carbonate a solubility well above 2.5 mol / l.
  • Li [BF 3 (CF 3 )] can be synthesized from an aqueous medium.
  • the salts according to the invention have an electrochemical stability comparable to that of LiPF 6 .
  • the borate salts produced according to the invention are therefore special suitable for use in electrochemical cells.
  • the borate salts can with other lithium salts or with borate complexes used in electrolytes for secondary lithium batteries.
  • the additives can also be used in electrolytes which contain lithium fluoroalkyl phosphates of the general formula (I) Li + [PF x (C y F 2y + 1-z H z ) 6-x ] - wherein 1 ⁇ x ⁇ 5 3 ⁇ y ⁇ 8 0 ⁇ z ⁇ 2y + 1 mean and the ligands (C y F 2y + 1-z H z ) may be the same or different, the compounds of the general formula (I '), Li + [PF a (CH b F c (CF 3 ) d ) e ] -
  • a is an integer from 2 to 5
  • b 0 or 1
  • c 0 or 1
  • d 2
  • e is an integer from 1 to 4
  • the conditions that b and c are not each simultaneously 0 and the sum of a + e is 6 and the ligands (CH b F c (CF 3 ) d ) are or can be different, except (DE 100 089 55).
  • the process for the preparation of lithium fluoroalkylphosphates of the general formula (I) is characterized in that at least one compound of the general formula H m P (C n H 2n + 1 ) 3-m OP (C n H 2n + 1 ) 3 Cl m P (C n H 2n + 1 ) 3-m F m P (C n H 2n + 1 ) 3-m Cl o P (C n H 2n + 1 ) 5-o F o P (C n H 2n + 1 ) 5-o in each of which 0 ⁇ m ⁇ 2, 3 ⁇ n ⁇ 8 and 0 ⁇ o ⁇ 4 means is fluorinated by electrolysis in hydrogen fluoride, the mixture of the fluorination products thus obtained is separated by extraction, phase separation and / or distillation, and the fluorinated alkylphosphorane thus obtained is reacted with lithium fluoride in an aprotic solvent or solvent mixture with exclusion of moisture, and the salt thus obtained of the general Formula
  • a BF 3 solvent complex is reacted 1: 1 with an alkyl lithium at temperatures below 0 ° C.
  • the mixture is slowly warmed to room temperature. Part of the solvent is removed and the solid is filtered off. The solid is purified in a conventional manner.
  • Another method for preparing the salts according to the invention is of lithium salts, which in a suitable solvent 1: 1 with known from the literature [B (CF 3) F 3] - (salts Lit: Chambers, J. Am Soc, 82.. , 5298 (1960)).
  • the mixture is stirred at elevated temperature and then filtered.
  • Aprotic non-aqueous solvents preferably solvents used in electrochemical cells, are added to the reaction mixture and dried.
  • borate salt of the invention can be obtained by the well-known from the literature [B (CF 3) F 3] - salt (Chambers, J.Am.Soc, 82, 5298) 1: 1 to 1: 1.5 is reacted with lithium salts and stirred in water at elevated temperature. The reaction mixture is heated at the boiling point for 0.5 to 2 hours, the water is removed and then suitable solvents, preferably solvents which are used in electrochemical cells, are added and dried.
  • the viscous, water-containing reaction mixture (contaminated with 15% LiBF 4 ) is dissolved in 50 ml of diethyl carbonate, dried with magnesium sulfate, mixed with 100 ml of CCl 4 after filtration and stirred.
  • the precipitated LiBF 4 is filtered off and the solution 19 F-NMR spectroscopy on BF 4 - controlled.
  • the diethyl carbonate removed together with CCl 4 is supplemented.
  • the solution is then brought to the desired concentration by further pumping off diethyl carbonate.
  • Lithium trifluoromethyl trifluoroborate is in acetonitrile at room temperature with tetraethylammonium chloride to tetraethylammonium trifluoromethyl trifluoroborate implemented.
  • the lithium chloride formed is filtered off and the product from acetonitrile / methyl tert. recrystallized butyl ether.
  • Lithium trifluoromethyl trifluoroborate is in acetonitrile at room temperature with tetraethylphosphonium chloride to tetraethylphosphonium Trifluoromethyl trifluoroborate implemented.
  • the lithium chloride formed is filtered off and the product of acetonitrile / methyl tert. butyl ether recrystallized.
  • the diethyl carbonate solution is dried with magnesium sulfate, filtered off, then mixed with 0.2 g of lithium carbonate (in order to neutralize HF present) and filtered off again (LiCO 3 and LiF are practically insoluble in diethyl carbonate).
  • the pH value is checked with indicator paper.
  • the content of the salt is determined by integration with 1,1-bis (trifluoromethyl) perfluorocyclohexane (bp 120 ° C).
  • the 1,1-bis (trifluoromethyl) perfluorocyclohexane is removed from the solution in a high vacuum.
  • a solution of 6.7 g of lithium bis (trifluoromethyl) difluoroborate in 22.8 g of diethyl carbonate is thus obtained.
  • Lithium bis (trifluoromethyl) difluoroborate is in acetonitrile at room temperature with tetraethylammonium chloride to tetraethylammonium Implemented bis (trifluoromethyl) difluoroborate.
  • the lithium chloride formed is filtered off and the product of acetonitrile / methyl tert. butyl ether recrystallized.
  • Figure 1 shows the first half cycles of the cyclic voltammograms.
EP01130618A 2001-01-24 2001-12-27 Sels de borates pour utilisation dans les cellules électrochimiques Withdrawn EP1229038A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10103189A DE10103189A1 (de) 2001-01-24 2001-01-24 Boratsalze zur Anwendung in elektrochemischen Zellen
DE10103189 2001-01-24

Publications (1)

Publication Number Publication Date
EP1229038A1 true EP1229038A1 (fr) 2002-08-07

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EP01130618A Withdrawn EP1229038A1 (fr) 2001-01-24 2001-12-27 Sels de borates pour utilisation dans les cellules électrochimiques

Country Status (10)

Country Link
US (1) US20020160261A1 (fr)
EP (1) EP1229038A1 (fr)
JP (1) JP2002305024A (fr)
KR (1) KR20020062832A (fr)
CN (1) CN1367174A (fr)
BR (1) BR0200169A (fr)
CA (1) CA2368990A1 (fr)
DE (1) DE10103189A1 (fr)
RU (1) RU2002101503A (fr)
TW (1) TW531925B (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1205480A3 (fr) * 2000-11-10 2003-03-26 MERCK PATENT GmbH Sels de tétrakisfluoroalkylborate et leur utilisation comme sels électrolytes
WO2005105815A1 (fr) * 2004-04-02 2005-11-10 Merck Patent Gmbh Liquides ioniques comprenant des anions fluoralkyltriffluorborate
WO2011015264A1 (fr) 2009-08-03 2011-02-10 Merck Patent Gmbh Système électrolytique
WO2012072218A1 (fr) 2010-11-30 2012-06-07 Merck Patent Gmbh Particule pour afficheurs et électrophorétiques
WO2013117284A1 (fr) 2012-02-08 2013-08-15 Merck Patent Gmbh Formulation de mésogènes réactifs contenant un additif conducteur

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10250808B3 (de) * 2002-10-31 2004-04-08 Honeywell Specialty Chemicals Seelze Gmbh Tetraalkylammoniumtetrafluoroborat-haltige Elektrolytzusammensetzung, Verfahren zur Herstellung dieser Tetraalkylammoniumtetrafluoroborathaltiger Elektrolytzusammensetzungen sowie deren Verwendung
DE112005003198B4 (de) * 2004-12-27 2014-02-06 National Institute Of Advanced Industrial Science And Technology Ionische Flüssigkeit
JP4861671B2 (ja) * 2005-10-05 2012-01-25 トヨタ自動車株式会社 リチウム塩およびその利用
WO2007063959A1 (fr) * 2005-12-02 2007-06-07 Kanto Denka Kogyo Co., Ltd. Liquide ionique contenant un cation phosphonium ayant une liaison p-n et son procede de production
GB0614486D0 (en) * 2006-07-21 2006-08-30 Add Power Technologies Ltd Electrolytes and Capacitors
US7820323B1 (en) 2006-09-07 2010-10-26 The United States Of America As Represented By The Secretary Of The Army Metal borate synthesis process
US8159815B2 (en) 2006-09-19 2012-04-17 Daihatsu Motor Co., Ltd. Electrochemical capacitor
DE102007027666A1 (de) * 2007-06-15 2008-12-18 Robert Bosch Gmbh Additive für Lithium-Ionen-Akkumulatoren
TW201145641A (en) * 2010-01-18 2011-12-16 Merck Patent Gmbh Compounds containing perfluoroalkyl-cyano-alkoxy-borate anions or perfluoroalkyl-cyano-alkoxy-fluoro-borate anions
JP6262932B2 (ja) * 2012-01-13 2018-01-17 積水化学工業株式会社 カルボン酸リチウム塩−三フッ化ホウ素錯体の製造方法
JP6228729B2 (ja) * 2012-06-29 2017-11-08 積水化学工業株式会社 カルボン酸リチウム塩−三フッ化ホウ素錯体の製造方法
FR3009439B1 (fr) * 2013-08-01 2017-08-25 Renault Sas Utilisation de borates comme inhibiteur de degradation des electrolytes organiques dans les accumulateurs electrochimiques
JP2017178964A (ja) * 2017-05-30 2017-10-05 積水化学工業株式会社 カルボン酸リチウム塩−三フッ化ホウ素錯体の製造方法
JP7346252B2 (ja) 2019-11-08 2023-09-19 株式会社日本触媒 非水電解液の製造方法及びリチウムイオン二次電池
CN112670581B (zh) * 2020-12-23 2023-11-17 远景动力技术(江苏)有限公司 适用于-20℃~60℃的非水电解液及基于其的锂离子电池

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JPH023052A (ja) * 1988-06-20 1990-01-08 Canon Inc 光硬化性組成物
EP1174941A2 (fr) * 2000-07-17 2002-01-23 Matsushita Electric Industrial Co., Ltd. Electrolyte nonaqueux et dispositif électrochimique contenant cet électrolyte

Patent Citations (2)

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Publication number Priority date Publication date Assignee Title
JPH023052A (ja) * 1988-06-20 1990-01-08 Canon Inc 光硬化性組成物
EP1174941A2 (fr) * 2000-07-17 2002-01-23 Matsushita Electric Industrial Co., Ltd. Electrolyte nonaqueux et dispositif électrochimique contenant cet électrolyte

Non-Patent Citations (9)

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Title
BOOTH, M. R. ET AL: "Reactivity of metal-metal bonds. VI. Cleavage reactions of (trimethyltin)pentacarbonyl-manganese", JOURNAL OF ORGANOMETALLIC CHEMISTRY (1970), 21(1), 171-80, XP001068526, ISSN: 0022-328X *
BRAUER, D. J. ET AL: "Vibrational spectra and normal coordinate analysis of CF3 compounds. XXXIV. The bis(trifluoromethyl)difluoroborate anion: x-ray structure of Cs[(CF3)2BF2]", JOURNAL OF ORGANOMETALLIC CHEMISTRY (1980), 192(3), 305-17, XP001068524, ISSN: 0022-328X *
BRAUER, DAVID J. ET AL: "Halogenation of (CF3)3B.cntdot.NH3: N,N-Dihaloamino- and Halo-tris(trifluoromethyl)borates [(CF3)3B-NX2]- and [(CF3)3B-X]-, X = F, Cl, Br", INORGANIC CHEMISTRY (6-9-1999), 38(18), 3972-3977, XP002195532, ISSN: 0020-1669 *
CHAMBERS, R. D. ET AL: "Some salts of trifluoromethylfluoroboric acid", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (1960), 82, 5298-301, XP000645306, ISSN: 0002-7863 *
CHAMBERS, R. D. ET AL: "The Trifluoromethylfluoroborate Anion", PROCEEDINGS OF THE CHEMICAL SOCIETY (1960), 114-5, XP001062040 *
FROHN, H.-J. ET AL: "A preparative method for perfluoroalkyltrifluoroborates and perfluoroalkyldifluoroboranes", ZEITSCHRIFT FUER ANORGANISCHE UND ALLGEMEINE CHEMIE (2001), 627(1), 15-16, XP001068334, ISSN: 0044-2313 *
HANDA M ET AL: "NEW LITHIUM SALT WITH A CHELATE COMPLEX OF PHOSPHORUS FOR LITHIUM BATTERY ELECTROLYTES", ELECTROCHEMICAL AND SOLID-STATE LETTERS, IEEE SERVICE CENTER, PISCATAWAY, NJ, US, vol. 2, no. 2, February 1999 (1999-02-01), pages 60 - 62, XP000864931, ISSN: 1099-0062 *
PATENT ABSTRACTS OF JAPAN vol. 014, no. 138 (P - 1022) 15 March 1990 (1990-03-15) *
PAWELKE, G. ET AL: "The bis(trifluoromethyl) difluoroborate anion", JOURNAL OF ORGANOMETALLIC CHEMISTRY (1979), 178(1), 1-4, XP000645199, ISSN: 0022-328X *

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1205480A3 (fr) * 2000-11-10 2003-03-26 MERCK PATENT GmbH Sels de tétrakisfluoroalkylborate et leur utilisation comme sels électrolytes
US6815119B2 (en) 2000-11-10 2004-11-09 Merck Patent Gmbh Tetrakisfluoroalkylborate salts and their use as conducting salts
WO2005105815A1 (fr) * 2004-04-02 2005-11-10 Merck Patent Gmbh Liquides ioniques comprenant des anions fluoralkyltriffluorborate
US8084617B2 (en) 2004-04-02 2011-12-27 Merck Patent Gmbh Ionic liquids having fluoroalkyltrifluoroborate anions
WO2011015264A1 (fr) 2009-08-03 2011-02-10 Merck Patent Gmbh Système électrolytique
CN102473527A (zh) * 2009-08-03 2012-05-23 默克专利有限公司 电解液体系
CN102473527B (zh) * 2009-08-03 2014-07-30 默克专利有限公司 电解液体系
US8920669B2 (en) 2009-08-03 2014-12-30 Merck Patent Gmbh Electrolyte system
WO2012072218A1 (fr) 2010-11-30 2012-06-07 Merck Patent Gmbh Particule pour afficheurs et électrophorétiques
US9182615B2 (en) 2010-11-30 2015-11-10 Merck Patent Gmbh Particles for electrophoretic displays
WO2013117284A1 (fr) 2012-02-08 2013-08-15 Merck Patent Gmbh Formulation de mésogènes réactifs contenant un additif conducteur

Also Published As

Publication number Publication date
RU2002101503A (ru) 2003-09-20
CA2368990A1 (fr) 2002-07-24
BR0200169A (pt) 2002-10-15
US20020160261A1 (en) 2002-10-31
DE10103189A1 (de) 2002-07-25
CN1367174A (zh) 2002-09-04
KR20020062832A (ko) 2002-07-31
TW531925B (en) 2003-05-11
JP2002305024A (ja) 2002-10-18

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